Upper West Side Homes for Sale

Located in Helena's Upper Westside's Mansion District, this remarkable 1912 residence offers a rare opportunity to become the owner of one of the city's most treasured historic homes. Available for the first time in nearly 60 years, this is a home that has been deeply loved, thoughtfully updated, and carefully preserved through generations. Designed by Robert Chambers Reamer, the renowned

Mary Ahmann Hibbard Helena Home Team

Stand-alone condo in a prime location at the base of Mount Helena! This spacious home features main-level living plus a full walk-out basement. The proximity to Mount Helena City Park provides abundant views and direct access to many miles of public trail systems. Enjoy the wonderful outdoor spaces providing views from the deck or shade from the covered patio. The perfect spot to live your best

Mark Stahly Big Sky Brokers, LLC

A beautifully preserved 1885 brick Victorian in Helena’s coveted Upper West neighborhood, just six blocks from the Tubbs Trailhead on Mount Helena. Over the past two years, this home has been carefully transformed with a soft white palette that highlights its original, intricate woodwork and fireplaces. Notable features include fresh paint, refinished and replica hardwood floors, a spacious

Freda Wilkinson Big Sky Brokers, LLC

Investment opportunity with many possibilities! Own a piece of Helena history while generating steady rental income. Located in the sought-after Mansion District, this classic Victorian has been converted into a fourplex, offering flexibility for both investors and owner-occupants. Rent all four units for maximum income, or easily combine two of the units to create a spacious owner's residence

Jeff Barber Keller Williams Capital Realty

A rare opportunity to own a true piece of Helena history, Appleton House #13—built in 1890 and proudly listed on the National Register of Historic Places. Situated on an expansive six city lots—nearly half an acre—this remarkable property offers a park-like setting in the heart of Helena. The outdoor space is nothing short of spectacular, featuring full fencing, underground sprinklers and drip

Freyja Bell Uncommon Ground, LLC

Investment Opportunity! Well-maintained duplex offering immediate rental income with both units currently occupied. Each unit features 2 bedrooms, 1 bathroom, functional layouts, and comfortable living spaces that appeal to long-term tenants. Pride of ownership is evident throughout, with consistent maintenance and care over the years.Owner currently provides lawn maintenance, helping

Cortney Senecal Keller Williams Capital Realty

Welcome home to 2565 Overlook Blvd, on Helena's westside. You'll find this 3bedroom 2.5 bathroom is super-convenient to Fort Harrison, Highway 12 West, the soon-to-be (rebuilt) Kessler School, and near Mount Helena too. On the main floor, you'll find slate influences throughout, an inviting fireplace and maintenance-free flooring within the living room, nice upgraded black granite countertops

Ryan Stavnes EXIT Realty of Helena

Brand-new construction for under $300,000—yes, it’s possible! Discover an affordable path to homeownership with these thoughtfully designed 2-bedroom, 1-bath condos offering 853 square feet of comfortable, efficient living. Located on Helena’s desirable Westside, you’ll enjoy convenient access to schools, hiking trails, recreation, and all the amenities of town. Blinds are included, and exterior

Julie Lamb-Heller Century 21 Heritage Realty - Helena

Wonderful Upper West Side cottage featuring a detached 2-car garage, hardwood floors, and retained 1950s charm. The main level offers 2 bedrooms, 1 bath, and a beautiful fireplace, all set at the base of Mt Helena.The lower level provides a clean slate for additional finished living space and offers potential for another bedroom, kitchen, and 1 bath. The property has been slated to be

Patrick Hern Bigfoot Realty Group

Welcome to 2650 Knight Street, a thoughtfully designed home that blends comfort, efficiency, and access to some of Helena’s best outdoor amenities.This Green Built property showcases energy efficient materials and construction, offering long term savings and a more sustainable lifestyle without compromising style or functionality.Inside, you’ll find a bright and inviting layout

Lisa Garrison Windermere Great Divide-Bozeman

NEW! $25,000 in seller concessions! What are concessions? Buyer choose to use funds toward remodel, closing costs/ prepaids or buy down rates! Home of JC Paulsen renowned architect of many Montana historical properties , including the original and stunning Montana Club, is on the market! Built in the 1800s, the stone facade and covered porches and balconies recall a bygone era. Irreplaceable

Lane Nygren Augustine Properties

Reflecting the real historical beginnings of Helena, the Adami Barn surely has stories to tell! Listen... can you hear them? One of a kind property nestled next to Helena's historic Reeder's Alley. One of Helena's earliest standing structures, this remarkable stone building was crafted in the 1870's from locally quarried stone, originally built as the Adami Barn. According to historical data, the

Cindy Stevick Cindy Stevick Real Estate

Brand-new construction for under $300,000—yes, it’s possible! Discover an affordable path to homeownership with these thoughtfully designed 2-bedroom, 1-bath condos offering 853 square feet of comfortable, efficient living. Located on Helena’s desirable Westside, you’ll enjoy convenient access to schools, hiking trails, recreation, and all the amenities of town. Blinds are included, and exterior

Julie Lamb-Heller Century 21 Heritage Realty - Helena

Nestled at the base of the iconic Mount Helena trail system, this luxury residential townhouse is located in an area that can never be duplicated. In the heart of Helena, the locale prides itself on historic homes, world class hiking/biking, restaurants, retail shops, galleries, museums, and breweries. Enjoy all the amenities of Helena, along with nearly 80 miles of trails and wilderness out the

Didi Peccia Augustine Properties

Price adjusted and rent increases coming October, projected to provide a 6.39% cap rate, with additional upside potential through further rent increases, as market conditions allow! Completed in 2019, this newer construction fourplex presents a rare opportunity to acquire a low maintenance multifamily asset with immediate income and future upside potential. Designed with tenant retention and

Bryanna Deschamps Millennium Real Estate & Management

Brand-new construction for under $300,000—yes, it’s possible! Discover an affordable path to homeownership with these thoughtfully designed 2-bedroom, 1-bath condos offering 853 square feet of comfortable, efficient living. Located on Helena’s desirable Westside, you’ll enjoy convenient access to schools, hiking trails, recreation, and all the amenities of town. Blinds are included, and exterior

Julie Lamb-Heller Century 21 Heritage Realty - Helena

Welcome to 804 Gilbert Street, a beautifully cared-for Victorian-style home in Helena’s sought-after Mansion District. Full of character and charm, this 3-bedroom, 2 1/2-bath home offers a great layout with many thoughtful updates while preserving the details that make a historic home special. Beautiful hardwood floors are featured throughout much of the home, complemented by tile in select

Wayne Woodland Big Sky Brokers, LLC

520 Madison Avenue, a well-loved home nestled in one of Helena’s cherished historic neighborhoods. Set along a beautiful tree-lined street, this home offers the character and charm Helena is known for, with downtown just minutes away. Enjoy convenient access to local shopping, restaurants, theaters, parks, and the sought-after Mount Helena trail system for hiking and mountain biking.The

Jennifer Swartz RE/MAX Of Helena

Welcome home—where location and ambiance meet in perfect harmony. This stunning 4,249 sqft., 5-bdrm, 3-bath custom-built home showcases quality finishes and timeless design throughout. An impressive entry welcomes you with classic white columns, a formal sitting area, and beautiful tile flooring that sets the tone for the elegance within. From the foyer, step into the open-concept living room

Joshua Koffler Coldwell Banker Mountainside Realty

This stunning Upper West Side residence boasts a million-dollar kitchen all on its own. Extensively remodeled in 2014 with a laser-focus on cooking, hosting, and entertaining, this home truly has it all. Industry-leading Viking appliances throughout, including three ovens, a gas cooktop grille, and a warming drawer, making Thanksgiving dinner effortless. A strategically positioned main sink, two

Cody Danielson Sherley Real Estate